I happened to be on Quora the other night and noticed a poster asking the question:

“What’s the best way to learn strategy?”

I thought it was a cool (and somewhat daunting) question, so I chimed in and wanted to share my answer here. It also occurred to me that learning strategic thinking has two common obstacles:

First, everything is – or at least can be – strategic (or approached strategically). Strategy, at its core, is a form of applied, holistic problem-solving. It’s more action verb than high concept – more of a cooking approach than a form of cuisine.

Second, is the classic decentralization problem: the really good, insightful bits are few and far between and scattered all over the place – both in life and on the internet. Jonathan and the OpenStrategy team have assembled a nice collection, but I felt like we could all benefit from more of that mentality.

So, going forward, I’m going to collect all my favorite works on strategy and list them here for anyone who’s interested in consuming or contributing. I’ll extend that to Github when I have time.

Ok, back to learning strategy.

As I’ve said previously, learning is an exercise in growing within a field of study across two dimensions: from theory to application, from big picture to technical detail, and the four “zones” they create when plotted against each other.

learning model for strategic thinking

Applied to strategy, broadly, that might look like:

how to learn strategy

But a learning path for strategic thinking gets a bit challenged when you recognize, as Martin Weigel sagely points out, strategy ultimately comes down to making good, long-term decisions:

“For if the mark of a strategy is a set of coherent actions driven by intent, it must follow that everything is strategic. Every moment represents a choice as to what to do in the world, and how to do it.” 

Put another way, strategy is really just an applied, goal-oriented form of logic.


So how do we become better long-term, goal-oriented thinkers?

To me there are four paths or vectors to learning strategy:

1. Reading

2. Observing

3. Doing

4. Mentorship

They all represent somewhat different experience conditions, but are also commonly related. If you have the good fortune of working from a great strategist s/he might coach you on a task and you’ve covered (2), (3) and (4) all at once.

They also map fairly well to the learning box model:

strategy reading learning and mentorship

This is an oversimplification, but in my personal experience, the best way to learn abstract and big picture strategy (theory, first principles, foundational concepts) is to (a) work with and get mentorship from great strategists and (b) follow and read great strategists.

As you move more toward the architectural, engineering and technical side of strategy, you’re likely to learn faster by (a) observing and watching strategists in action and/or (b) honestly just taking the plunge yourself and figuring it out as you go along. Whether or not you can find an experienced mentor, focus on the area of strategy you want to pursue and push ahead on a project.

Want to learn business strategy? Start a small business.

Want to learn digital or marketing strategy? Start a blog or social media presence and try to grow it.

Want to learn game theory? Learn to play chess or poker and build from there.

As Winston Churchill said: “Success is not final; failure is not fatal: it is the courage to continue that counts.”

This could not be more true in strategy.

And, as you progress, each of the four discipline areas will begin to mutually reinforce one another, while synthesizing across them becomes faster and clearer.

The second element to growing as is a strategist comes down to improving your long-term judgement skills generally.

Research tells us there are a few recommended ways to approach this:

1. Regularly carve out space. Consistently schedule at least day or afternoon off once a month to detach yourself from your work completely. Spend some time thinking about it in a new setting, reading or focused on something completely different. Numerous studies show spaced repetition and frequency improves creativity, learning retention and emotional intelligence. Off-sites work. Long walks work. Vacations work.

2. Act like an outside observer. A recent study in the Journal of Psychological Science shows when people think about relationship conflict from a first-person perspective, their judgement suffers. When they try to evaluate the same conflict from a third-person perspective, their judgement improves. If you’re having trouble fully breaking away, involve a friend, family-member or trusted advisor. At a group or population-level, this also has very interesting implications for democracy, voting and governance.

3. Broaden your focus or get more options on the table. Therese Houston, a psychology Ph.D. and author of How Women Decide – What’s True, What’s Not, and What Strategies Spark the Best Choices, sees artificially-imposed constraints as one of the biggest natural barriers to better judgement. One of her simple judgement hacks – which extends to strategy – is forcing yourself to always come up with three scenarios or options every time you need to make an important decision. Simply the process of conceptualizing and framing three different choices – and their trade-offs – objectively improves decision-making.

There, I gave you three choices. Better already, right?

And finally, play games. Whether it’s chess, poker or role-playing and simulation games, game theory is an Olympic-level training ground for growing and developing as a strategic thinker.

learn game theory 

game theory strategic building blocks

At the end of the day, becoming a better strategic thinker is a lifelong journey. Strategy requires sound decision-making, as well as the ability to anticipate and adapt to change.

That will always be more of a journey than a destination.

And for anyone looking to take their next steps, I’d recommend starting here.

If you found this helpful, share it with a friend, teammate or your network

2 thoughts on “How to Learn Strategy (When Everything is Strategic)

  1. I would like to recommend ‘Good Strategy Bad Strategy’ by Richard Rumelt and ‘Superforecasting’ by Philip Tetlock and Dan Gardner.

  2. Either a person is a strategic thinker from his birth or he can learn the required skills to turn out to be a great strategic Solomon. Yes, it is possible for an individual to develop the talent of strategic thinking. Yes, your leadership success depends on your strategic thinking potentiality. Immersion, apprenticeships, simulation, game-theory training, case-based education, cognitive reshaping- are some of the proven methods that help you to develop your shrewd thinking potentiality. You only need the guidance to follow this approach successfully. From my suggestion, you should engage yourself in executive coaching to find the direction you want for the growth of your strategic thinking preparedness.

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